Amphophilic cationic polymers are useful as general polymeric surfactants. These cationic polymers find applications as water treatment chemicals, membranes, pigment dispersants, coupling agents, and antistats. Anionic amphophilic polymers can be used to complement or replace the cationics in these applications.
In accordance with this invention, the hydrophosphonylation of allyl glycidyl ether polymers with sodium hypophosphite is a successful route to making a novel class of anionic polymers. The chemistry involved in this reaction is the addition of sodium hypophosphite to an olefin to give a sodium alkyl phosphonite. This reaction is general for phosphorous compounds containing a P--H bond.
The reaction of sodium hypophosphite to a monomeric olefin to give a sodium alkyl phosphonite is known in the art and described in Organic Reactions, Vol. 13, F. W. Stacey, and J. F. Harris, p 218 (1963). A description of the addition of sodium hypophosphite to octene-1 is given in British Pat. No. 660,918. USSR Pat. No. 596,593 describes the hydrophosphonylation of allyl cellulose polymers, however, water soluble allyl glycidyl ether polymers are not among those described. The polymers disclosed in the USSR Pat. No. 596,593 are described as being water resistant; ergo water insoluble. The optimization of the reaction of sodium hypophosphite with octene-1 is discussed by C. Herranz Augustin, Tenside Detergents, Volume 18, pages 190-193 (1981).
The prior art does not disclose high molecular weight hydrophosphonylated polymers which exhibit good water solubility and dispersant properties. It is the object of the present invention to prepare hydrophosphonylated glycidyl ether polymers and copolymers which are water soluble and which are effective aqueous dispersing agents. It is known that polymeric suspending agents are more efficient than the monomeric types. The polymeric materials are also more effective as thickeners, and are resistant to solvent extraction when used as stabilizers in polymer formulations.
The technical literature lists many applications for hypophosphorous acid, sodium hypophosphite, and their derivatives. These references provided good indications of the utility of hydrophosphonylated polymers. For example, a major use of sodium hypophosphite is for the electroless deposition of nickel as disclosed in Kirk-Othmer Encyclopedia of Chemical Technology, 3rd Edition, Volume 10, p. 249. Sodium hypophosphite derivatives are disclosed as dispersing agents and anti-fouling agents in vinyl chloride polymerization in U.S. Pat. No. 3,026,308 and Ger. Offen. No. 2,611,385. References also disclose the usefulness of phosphonites as polyvinyl chloride (PVC) stabilizers (see for example, U.S. Pat. No. 3,050,499). This would give the hydrophosphonylated polymers of this invention utility as stabilizers for PVC.
Hydrophosphonylated polymers are highly hygroscopic. This property makes them suitable for use as anti-static agents. For some applications, the use of hydrophosphonylated polymers have distinct advantages over the commonly used cationics, such as the cationic quaternary ammonium salts. Unlike the quaternary ammonium salts, the hydrophosphonylated polymers are colorless and do not break down to colored or basic amine compounds. This makes the hydrophosphonylated polymers particularly useful as antistats in polyvinyl chloride resins.